See all properties
Entire home

Harbor Cottage at the Chesapeake Bay - Dog Friendly Beach

Photo gallery for Harbor Cottage at the Chesapeake Bay - Dog Friendly Beach

Deck with awning and a Harbor View
Boats and Autumn Leaves - thanks to guest Laura Friend, Photographer
Fun for kids as the water is shallow.
Living room opens onto deck; sofa unfolds to full size bed.
Dining area, opens onto deck; table expands for seating for 10!

Reviews

9.8 out of 10
Exceptional
2 bedrooms2 bathroomsSleeps 592.9 sq m

Popular amenities

  • Parking available
  • Kitchen
  • Barbecue grill
  • Pet-friendly
  • Outdoor space
  • Air conditioning

Explore the area

Map
St Leonard, MD
  • Matoaka Beach
    ‪14 min walk‬
  • Calvert Cliffs State Park
    ‪17 min drive‬
  • Cove Point Lighthouse
    ‪21 min drive‬
  • Leonardtown, MD (LTW-St. Marys County)
    ‪29 min drive‬

Rooms & beds

2 bedrooms (sleeps 5)

Convertible bed(s)

1 Double Futon

2 bathrooms

Bathroom 1

Bathtub or shower · Toilet

Bathroom 2

Bathtub or shower · Toilet

Spaces

Deck or patio
Kitchen
Dining area

About this property

Harbor Cottage at the Chesapeake Bay - Dog Friendly Beach

Harbor Cottage. Relax on the deck overlooking the fishing and sailboats of Flag Harbor opening onto the Chesapeake Bay. Only a three minute walk to the big sand beach famous for fossils from the Miocene period. Very quiet and not crowded. Great fishing from the beach or charter a boat. Shallow water makes for great swimming for kids. Bring your well behaved dog to enjoy the beach and swimming with you.
Due to the pandemic we have kept a vacant day between renters as a courtesy to our cleaners and our arriving guests. These dates are blocked on our calendar.

Washington DC or Annapolis is only one hour away, and the entire Chesapeake Bay area is steeped in American history. Just 15 minutes from the shops and restaurants of Solomons Island, and the terrific Marine Museum there. Many state parks for hiking and birdwatching.
PLEASE CONTACT ME BEFORE CLICKING "BOOK IT NOW"
Keywords: Vacation Rental Cottage, Beach House, dog

Property manager

Katherine Nelson

Languages

English

Add dates for prices

Amenities

Kitchen
Pet-friendly
Air conditioning
Outdoor space
Parking available
Water view

Have a question?

AI iconBeta

Get instant answers with AI powered search of property information and reviews.

Similar properties

Beach

Spring Getaway Beach Combing & Relaxation

  • Kitchen
  • Washer
  • Dryer
  • Pet-friendly
9.6 out of 10, (21 reviews)
Spring Getaway Beach Combing & Relaxation

House Rules

Check in after 3:00 PM
Minimum age to rent: 25
Check out before 11:00 AM
default

Children

Children allowed: ages 0–17
Parents are responsible for toddler-proofing
default

Events

No events allowed
Seating for 10 at the dining table. Ask me.
default

Pets

Pets allowed: dogs (limit 2 total)
Well behaved dogs are welcome. Add $35. per dog.
default

Smoking

Smoking is not permitted
Well behaved dogs only - please pad the floor under the crate to protect the hardwood floor. Contact me if your dog as ever bitten man or beast.
Our beach is unguarded - swim, fish, and boat at your own risk. Clean-up after yourself and your dog on the beach and neighborhood. No fireworks.
Stay off the cliffs - they are a landslide danger and private property. Fossil hunt at the water line or in the surf for better results and safety.

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Note from host: Seating for 10 at the dining table. Ask me.
Long-term renters welcome
Host has indicated that there are no carbon monoxide detectors or gas appliances on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit and a deadlock

We should mention

A car is required for transport to and from this property

About the area

St. Leonard

Located in St. Leonard, this cottage is on the waterfront. Flag Harbor Marina and Perigeaux Vineyards and Winery are worth checking out if an activity is on the agenda, while those wishing to experience the area's natural beauty can explore Battle Creek Cypress Swamp Sanctuary and Calvert Cliffs State Park. R&J's PlayPark and Annmarie Sculpture Garden and Arts Center are also worth visiting. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
Map
St Leonard, MD

What's nearby

  • Matoaka Beach - 14 min walk - 1.2 km
  • Jefferson Patterson Park and Museum - 16 min drive - 14.1 km
  • Calvert Cliffs State Park - 17 min drive - 16.3 km
  • Cove Point Lighthouse - 21 min drive - 21.4 km
  • Patuxent River Naval Air Station - 33 min drive - 37.0 km

Getting around

  • Ronald Reagan National Airport (DCA) - 73 min drive

Restaurants

  • ‪Adams Taphouse and Grille - ‬11 min drive
  • ‪Vera's White Sands Beach Club - ‬17 min drive
  • ‪Gateway Restaurant & Lounge - ‬12 min drive
  • ‪The Tavern - ‬5 min drive
  • ‪Frying Pan - ‬14 min drive

Frequently asked questions

Is Harbor Cottage at the Chesapeake Bay - Dog Friendly Beach pet-friendly?

Yes, this property allows dogs (limit 2 total).

What time is check-in at Harbor Cottage at the Chesapeake Bay - Dog Friendly Beach?

Check-in begins at 3:00 PM.

What time is check-out at Harbor Cottage at the Chesapeake Bay - Dog Friendly Beach?

Checkout is at 11:00 AM.

Where is Harbor Cottage at the Chesapeake Bay - Dog Friendly Beach located?

Situated on the waterfront, this cottage is within a 15-minute walk of Long Beach, Flag Harbor Marina and Matoaka Beach. Flag Ponds Nature Park is 0.7 mi (1.2 km) away.

Reviews

9.8

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 130 out of 152 reviews
Rating 8 - Good. 20 out of 152 reviews
Rating 6 - Okay. 1 out of 152 reviews
Rating 4 - Poor. 1 out of 152 reviews
Rating 2 - Terrible. 0 out of 152 reviews

9.4/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

8/10 Good

David S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Short but sweet trip.

Our annual trip with our grand kids (5 and 10) on their spring break. We always try to go some place new but within an hour or so from their home near Alexander. This place fit us wonderfully! Kids had a ball! Loved the beach- easy walk! Too cold to swim but they loved the sand. Lots of special yhings to do in the area with a short drive. Kitchen was awesome, well stocked and clean. Not much yard to play in but didn’t need it with beach.
Stayed 5 nights in Apr 2025

10/10 Excellent

Steve M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Calvert Cliff's Refuel

Stayed here for about 3 weeks for a short term work assignment, very clean and pretty well stocked. No issues, I'd stay again.
Stayed 20 nights in Feb 2025

10/10 Excellent

eileen m.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Always a Delight

We've had the pleasure of staying at Harbor Cottage multiple times. It's charm and location can't be beat. It is always spotlessly clean and has a cozy beachy feel. In a quiet neighborhood, right across a private lane from picturesque Flag Harbor, it's peaceful and feels out of the way, but is only a few minutes drive to area attractions like Calvert Cliffs and Solomons. The dog friendly community beach is 1/2 block walk (or drive) down the lane. We have spent hours there searching for fossil shark teeth, or just watching the bald eagles and ospreys fly. If you are visiting the area do yourself a favor and stay at Harbor Cottage!
Stayed 4 nights in Dec 2024

10/10 Excellent

Gloria V.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect beachside retreat

This house was the perfect fit for our stay in st Leonard. The kitchen was well appointed and the facility was very comfortable. We would definitely stay here again.
Stayed 4 nights in Nov 2024

10/10 Excellent

Steve D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing property we loved it

I will be back next year this location was great.
Stayed 5 nights in Oct 2024

10/10 Excellent

JoAnne M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Relaxing stay

This is a lovely home that is well equipped for all your needs. The kitchen has everything and there are many beach chairs to use at the beach a short walk away. You will have a parking pass if you would rather not walk.wouldrathernot not walk.
Stayed 5 nights in Oct 2024

10/10 Excellent

Nick G.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great location

My mother loved the harbor and beach that was right there.
Stayed 7 nights in Oct 2024

10/10 Excellent

Cathy H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Recharge and Tranquility

This is our third year staying at this serene and peaceful property. Although the weather was dismal it did not deter us from enjoying a recharging and tranquil week. We will definitely be back next year and many more years to follow. Thanks for the memories!
Stayed 4 nights in Sep 2024

10/10 Excellent

jason s.

Liked: Cleanliness, check-in, communication, location, listing accuracy

perfect

been staying at this perfect setting for years. ownership always gracious hosts. couldn't find a rental with better neighbors and accessibility to beach. look forward to next year.
Stayed 14 nights in Sep 2024

10/10 Excellent

Suzi S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Lovely

I really enjoyed the area and property
Stayed 7 nights in Aug 2024

10/10 Excellent

susan d.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beach heaven

This was an amazing trip. The cottage is just perfect. The beach is wonderful. I wouldn’t change a thing. Thank you.
Stayed 21 nights in Jun 2024

10/10 Excellent

AMJ v.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Thank you!

We really enjoyed our stay at this charming cottage. Thank you for hospitality!
Stayed 9 nights in Jul 2024

8/10 Good

Thomas C A.

Liked: Cleanliness, check-in, communication, listing accuracy

Very clean dog friendly

The cottage was very clean and had everything we needed for a wonderful stay. The not-to-crowded beach is just a 2 minute walk away. Only disappointment for us was no outdoor private area with the dogs. Lots of traffic, cars, adults with and without dogs, and kids passing the front of the property all hours of the day. This is not a good location if your furry child is an anxious barker.
Stayed 5 nights in Jun 2024

8/10 Good

Thor S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Private Beach Access!

This was our second stay at Harbor Cottage and the private, dog-friendly beach access this property provides is wonderful! (and for us makes up for no washer or dryer). The kitchen appliances are all nice and in working order (the microwave is brand new!) as is the heat and ac. The weather was so pleasant we were able to turn the hvac system off and open all the windows to let in much needed fresh air and even more appreciated bay breezes. Communications are excellent with the host/owner as well as the property manager who resides in the same community. The neighborhood is both quiet and quaint and everyone is extremely friendly, all the neighbors look out for one another. Parking is definitely limited to two vehicles and out of necessity access to the beach during warm weather weekends is closely restricted to vehicles with community passes which is a huge plus.
Stayed 5 nights in May 2024

10/10 Excellent

Brian N.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Another great visit

This is our 3rd time staying at the property. We had a great time, the house was great and the location can’t be beat. Thanks!
Stayed 4 nights in May 2024

10/10 Excellent

Brian S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful place to stay!

Wonderful place for a family get away. The house is perfect to spend time with family… it has a great open layout and a full bathroom for each of the bedrooms. The house is also clean, and the heat and air conditioning worked great. There is a nice view of boats out the front windows, and the beach was a very short walk away. I highly recommend this properly.
Stayed 4 nights in May 2024

10/10 Excellent

eileen m.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Always Delightful

Another wonderful stay at Harbor Cottage! The location, the neighborhood and access to the beach and activities can't be beat. The host is very thoughtful and a great communicator.
Stayed 6 nights in Apr 2024

10/10 Excellent

Janice K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Scenic views and close to hiking

This cute cottage was fully stocked and located convent to beautiful hiking areas and preserves. When not hiking I could take a stroll to the dog friendly beach just a 3minute walk. Owner was easy to communicate with.
Stayed 6 nights in Mar 2024

10/10 Excellent

Matthew C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Rented for business travel

This was our second time renting the property. Everything was clean and as expected. Quiet area and easy walk to the beach.
Stayed 18 nights in Feb 2024

10/10 Excellent

Thor S., Western Carolinas

Liked: Cleanliness, check-in, communication, location, listing accuracy

A Gem and Already Booked Again!

Having lived in So. MD for over 50 years before moving away, sadly, we had to return for the funeral of a dear and immediate family member. However; our stay at “Harbor Cottage on the Chesapeake w Dog Friendly Beach” wound up transforming our stay from sorrowful to one filled with great memories walking our dog and grandchildren along the beach and then enjoying the idyllic marina views off the front deck of the house. The neighborhood is a QUIET and CLEAN one and EVERYONE is extremely friendly. Best of all, it was a huge stress reducer to checkin to a rental rated for cleanliness that was actually …. clean! Terrific communications by and from the owners, also. We so enjoyed our stay at “Harbor Cottage on the Chesapeake w Dog Friendly Beach” we have already booked a return visit!
Stayed 4 nights in Jan 2024

10/10 Excellent

susan d.

Liked: Cleanliness, check-in, communication, location, listing accuracy

moms funeral

the cottage was just perfect thanks for everything.
Stayed 4 nights in Oct 2023

10/10 Excellent

Tara M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

October 2023 stay

Great location very close to beach(s) and with 15 -20 mins of stores, restaurants, Calvert cliffs and the marine museum.
Stayed 4 nights in Oct 2023

10/10 Excellent

eileen m.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Love Staying at Harbor Cottage

Another great stay. The location and charm of Harbor Cottage can't be beat if you are going to the Calvert Cliffs area! Katherine is a wonderful host.
Stayed 4 nights in Sep 2023

10/10 Excellent

jason s.

Liked: Cleanliness, check-in, communication, location, listing accuracy

2nd Year

Looking forward to staying again next Summer.
Stayed 14 nights in Sep 2023

10/10 Excellent

Cathy H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Becoming an Annual Event!

This is the second year, my best friend of 20 plus years and my almost 13 year old "love bug" American Cocker Spaniel -Emmy Lou-have enjoyed the peaceful and serenity of this hidden gem. I would rate this as a 10 plus!
Stayed 4 nights in Sep 2023

About the host

Hosted by Katherine Nelson

Host profile image
We love this area for a quick get-a-way: our neighbors are friendly and helpful, and the beach is peaceful and beautiful! We enjoy watching the eagles and ospreys fish, and the large schools of fish that can be seen in the (usually) clear water.

Why they chose this property

We found this peaceful and friendly spot by chance - it's so close to the Washington DC area. The community is very dog-friendly, and when we are alone on the beach, they can romp in the waves off the leash. There aren't dangerous tides, and seldom rough water.

What makes this property unique

We have discovered the fun of fossil hunting, or just sitting at the beach and reading and re-charging our energies. The light, wind, and water are constantly changing. You can walk the beach for hours.

Languages:

English
Tell us how we can improve our siteShare feedback